1-Methylpiperazine → HCID 4900060, compound

HRID 1729018Notes

Reaction equation

HRID 1729018 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([OH:12])=O)[CH:3]=[CH:2]1.[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>CN(C)C=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([N:17]2[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]2)=[O:12])[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 742811H-Indole-7-carboxylic acid

Product 1

HCID 4900060HCID 4900060, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Indole-7-carboxylic acid (3.20 g, 0.020 mole) was dissolved in 30 ml of dimethylformamide (DMF) and chilled with an ice-water bath. N,N'-Carbonyldiimidazole was added (3.3 g, 0.020 mole) and the reaction mixture was stirred for 1 hour in the cold. At the end of this time N-methylpiperazine was added (2.5 g, 0.025 mole) and the reaction was allowed to come to room temperature overnight (about 16 hours). The DMF was removed under reduced pressure and the residue was passed over a column of basic alumina (50% methanol-ether) to remove residual imidazole.Recrystallization of the product from CH2Cl2 -pentane gave 2.35 g (48%) of 1-(1H-indole-7-ylcarbonyl)-4-methylpiperazine, m.p. 176°-178° C.

Workup

  1. temperaturechilled with an ice-water bath
  2. waitto come to room temperature overnight
  3. custom(about 16 hours)
  4. customThe DMF was removed under reduced pressure
  5. customto remove residual imidazole
  6. customRecrystallization of the product from CH2Cl2 -pentane

Sources & evidence

ORD record
ord-78f449863a1b435eabed509b7056d340
Source dataset
uspto-grants-1994_07
Patent number
US05330986

Reaction notes

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